Metal Complexes

Abstract

The invention relates to novel metal complexes which can be used as functional materials in a series of different applications that can associated with the electronics industry in the broadest sense. The inventive compounds are described by formulas (1) and (1a).

1 - 19 . (canceled) 
     
     
         20 . A compound of the formula (1)
   M(L) n (L′) m (L″) o   Formula (1)   
       wherein M(L) n  comprises a sub-structure of the formula (2) 
       
         
           
           
               
               
           
         
       
       wherein
 M is on each occurrence iridium, platinum, palladium, gold, tungsten, rhenium, ruthenium, or osmium; 
 D is, identically or differently on each occurrence, an sp 2 -hybridized heteroatom having a non-bonding electron pair which coordinates to M; 
 C is on each occurrence an sp 2 -hybridised carbon atom which bonds to M; 
 E is, identically or differently on each occurrence, an sp 2 -hybridised carbon or nitrogen atom; 
 Y is, identically or differently on each occurrence, CR 2 , C(═O), C(═NR), C(═N—NR 2 ), C(═CR 2 ), SiR 2 , O, S, S(═O), S(═O) 2 , Se, NR, PR, P(═O)R, AsR, As(═O)R, or BR; 
 Cy1 is, identically or differently on each occurrence, an optionally R 1 -substituted homo- or heterocycle which bonds to M via an sp 2 -hybridised carbon atom; 
 Cy2 is, identically or differently on each occurrence, an optionally R 1 -substituted heterocycle which coordinates to M via the atom D; 
 R is, identically or differently on each occurrence, H; F; CN; a straight-chain alkyl or alkoxy group having up to 40 C atoms; a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms; wherein one or more non-adjacent CH 2  groups of said straight-chain alkyl or alkoxy groups or branched or cyclic alkyl or alkoxy groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , —O—, —S—, —NR 2 —, —(C═O)—, —(C═NR 2 )—, —P═O(R 2 )—, or —CONR e — and wherein one or more H atoms of said straight-chain alkyl or alkoxy groups or branched or cyclic alkyl or alkoxy groups are optionally replaced by F; or an aromatic or heteroaromatic system or an aryloxy or heteroaryloxy group having up to 30 C atoms optionally substituted by one or more radicals R 1 ; and wherein two R optionally define an aliphatic or aromatic ring system; 
 R 1  is, identically or differently on each occurrence; H; F; Cl; Br; I; OH; NO 2 ; CN; N(R 2 ) 2 ; a straight-chain alkyl or alkoxy group having up to 40 C atoms; a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms; wherein one or more non-adjacent CH 2  groups of said straight-chain alkyl or alkoxy groups or branched or cyclic alkyl or alkoxy groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 —O—, —S—, —NR 2 —, —(C═O)—, —(C—NR 2 )—, —P═O(R 2 )—, —COOR 2 —, or —CONR 2 — and wherein one or more H atoms of said straight-chain alkyl or alkoxy groups or branched or cyclic alkyl or alkoxy groups are optionally replaced by F; or an aromatic or heteroaromatic system or an aryloxy or heteroaryloxy group having up to 30 C atoms substituted by one or more non-aromatic radicals R 1 , wherein a plurality of R 1 , either on the same ring or on different rings, optionally define a mono- or polycyclic, aliphatic or aromatic ring system; 
 R 2  is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms; 
 n is 1,2, or 3; 
 L′ and L″
 are monoanionic, bidentate-chelating ligands; and 
 
 m and o
 are, identically or differently on each occurrence, 0, 1, or 2. 
 
 
     
     
         21 . The compound of  claim 20 , wherein Cy1 and Cy2 are aromatic or heteroaromatic systems. 
     
     
         22 . The compound of  claim 21 , wherein M(L) n  comprises a sub-structure of the formula (2a) 
       
         
           
           
               
               
           
         
       
       wherein
 D is, identically or differently on each occurrence, nitrogen or phosphorus; 
 X is, identically or differently on each occurrence, CR 1 , N, or P; or (X—X) or (X═X) is NR 1 , S, or O; or if E in the corresponding ring is N, (X—X) or (X═X) is CR 1 , N, or P; and 
 E is, identically or differently on each occurrence, C or N, with the proviso that if the E is N, precisely one unit X—X in the corresponding ring is CR 1 , N, or P. 
 
     
     
         23 . The compound of  claim 22 , wherein M(L) n  comprises at least one sub-structure of the formula (2b) 
       
         
           
           
               
               
           
         
       
       and optionally further comprises a sub-structure M(L′) n  of the formula (3) 
       
         
           
           
               
               
           
         
       
       wherein
 X is, identically or differently on each occurrence, CR 1 , N, or P; or (X—X) or (X═X) is NR 1 , S, or O; and 
 A is, identically or differently on each occurrence, —CR 1 ═CR 1 —, —N═CR 1 —, —P═CR 1 —, —N═N—, —P═N—, NR 1 , O, or S; 
 
       with the proviso that each of the two rings is a five- or six-membered ring. 
     
     
         24 . The compound of  claim 20 , wherein monoanionic, bidentate ligands L″ are selected from the group consisting of 1,3-diketonates derived from 1,3-diketones, 3-ketonates derived from 3-ketoesters, carboxylates derived from aminocarboxylic acids, salicyliminates derived from salicylimines, and borates of nitrogen-containing heterocycles. 
     
     
         25 . The compound of  claim 20 , wherein n is 2 or 3. 
     
     
         26 . The compound of  claim 25 , wherein m and o are 0. 
     
     
         27 . The compound of  claim 20 , wherein Y is CR 2 , C(═O), C(═CR 2 ), O, S, NR, PR, P(═O)R, or BR. 
     
     
         28 . The compound of  claim 27 , wherein L is a spiro compound and Y is CR 2 , wherein the C of said CR 2  is a spiro atom. 
     
     
         29 . The compound of  claim 27 , wherein L is a derivative of azaspirobifluorene. 
     
     
         30 . The compound of  claim 20 , wherein D is N. 
     
     
         31 . The compound of  claim 20 , wherein X is CR 1 . 
     
     
         32 . A process for preparing the compound of  claim 20  comprising reacting the corresponding free ligands with metal alkoxides of the formula (4), with metal ketoketonates of the formula (5) or mono- or polynuclear metal halides of the formulae (6), (7), or (8) 
       
         
           
           
               
               
           
         
       
       wherein p is 1 for divalent metals, p is 2 for trivalent metals, and Hal is F, Cl, Br, or I. 
     
     
         33 . The process of  claim 32 , wherein metal compounds which carry alkoxide and/or halide and/or hydroxyl radicals and also ketoketonate radicals are used, wherein said metal compounds are optionally charged. 
     
     
         34 . A conjugated, partially conjugated, or non-conjugated oligomer, polymer, or dendrimer comprising one or more compounds according to  claim 20 , wherein at least one of R and R 1  represents a bond to the polymer or dendrimer. 
     
     
         35 . The conjugated, partially conjugated, or non-conjugated oligomer, polymer, or dendrimer of  claim 34 , wherein said conjugated, partially conjugated, or non-conjugated oligomer, polymer, or dendrimer is selected from the group consisting of polyfluorenes, polyspirobifluorenes, polydihydrophenanthrenes, polyindenofluorenes, polyphenanthrenes, poly-para-phenylenes, polycarbazoles, polyketones, polysilanes, polythiophenes, and copolymers thereof. 
     
     
         36 . An organic electronic component comprising one or more compounds according to  claim 20 . 
     
     
         37 . An organic electronic component comprising one or more conjugated, partially conjugated, or non-conjugated oligomer, polymer, or dendrimer according to  claim 34 . 
     
     
         38 . The organic electronic component of  claim 36 , wherein said component is selected from the group consisting of organic and polymeric light-emitting diodes, organic field-effect transistors, organic thin-film transistors, organic integrated circuits, organic solar cells, organic light-emitting transistors, organic field-quench devices, light-emitting electrochemical cells, and organic laser diodes. 
     
     
         39 . The organic electronic component of  claim 37 , wherein said component is selected from the group consisting of organic and polymeric light-emitting diodes, organic field-effect transistors, organic thin-film transistors, organic integrated circuits, organic solar cells, organic light-emitting transistors, organic field-quench devices, light-emitting electrochemical cells, and organic laser diodes.